Holiday rentals with outdoor seating in Chesterton

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Chesterton

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Top Guest favourite
A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.
Farm stay in La Porte
4.99 out of 5 average rating, 523 reviews

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Guest favourite
A sandy pathway winds through tall grasses, leading to Lake Michigan. The tranquil water reflects the soft hues of the sky, with clouds adding texture to the serene scene. The beach's inviting atmosphere creates a perfect setting for relaxation and exploration.
Home in Porter
4.91 out of 5 average rating, 121 reviews

Blue Birdhouse - Indiana Dunes

Welcome to The Birdhouse - Your Perfect Getaway! 🐦🌿 Nestled near the Indiana Dunes National Lakeshore, our cozy 2-bedroom, 1-bathroom home is perfect for families, couples, and nature lovers. Enjoy a pet-friendly, fully fenced yard, free parking for 2 vehicles, a fully equipped kitchen, laundry, and a BBQ grill with patio for outdoor dining. Minutes from Lake Michigan beaches, hiking trails, and local dining, it’s the ideal spot for beachgoers and adventurers. Book your stay today! 🌞🏖️🌳

Guest favourite
A multi-level house is set on a grassy area, featuring a stairway leading to a deck adorned with flower pots. Vibrant red canopies provide shade, and bicycles are stationed nearby, creating an inviting environment. The exterior showcases a mix of wooden and painted surfaces.
Home in Chesterton
4.83 out of 5 average rating, 386 reviews

South Shore Studio Apartment {National Park}

I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

Top Guest favourite
A bright living room is showcased with large windows allowing natural light to fill the space. A plush beige sofa is paired with two striped armchairs, accented by decorative cushions. A white coffee table rests on a textured area rug, enhancing the room's warm atmosphere.
Apartment in Valparaiso
4.99 out of 5 average rating, 173 reviews

ValpoVilla: Location, location, location!

Located in the heart of downtown Valparaiso, guests will love this updated, historic charmer! Walk to fabulous restaurants, local shops, or breweries & wineries in minutes. This unit has been fully updated and fully stocked with room to sleep 6. You'll be 25 minutes from the beaches of Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking orchards. This space is perfect for families & friends who want to relax or adventure outdoors!

Top Guest favourite
A charming blue exterior of the home features a welcoming yellow front door. A wooden pathway leads to the entrance, bordered by vibrant flower beds. Two yellow chairs are positioned on the porch, alongside well-kept greenery that enhances the inviting appearance.
Home in Michigan City
4.91 out of 5 average rating, 102 reviews

Michigan City Indiana Dunes Beach National Park

Escape to our cozy home just minutes from the stunning Indiana Dunes National Park! Located in the heart of Michigan City, this charming retreat offers a relaxing getaway Enjoy a well-furnished living area, a fully equipped kitchen, and 2 comfortable bedrooms. Outdoor Bliss: Relax on the private deck or explore our beautiful garden—ideal for unwinding. Adventure Awaits: Only a short drive from the park's sandy shores, hiking trails, Lake Michigan. **CONTACT US FOR SEASONAL DISCOUNTS**

Top Guest favourite
Guesthouse in Chesterton
4.96 out of 5 average rating, 198 reviews

Bro’s Place 6 mile drive to Indiana Dune’s

Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

Guest favourite
An outdoor space is presented with a patio featuring a round table and four chairs under a red umbrella. A fire pit is positioned nearby, with a pile of branches placed in the foreground. The area is enclosed by a wooden fence with decorative artwork visible.
Guesthouse in Chesterton
4.91 out of 5 average rating, 399 reviews

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Couch opens into a full size bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall.

Guest favourite
A modern kitchen space is presented, featuring a large dining table accompanied by black chairs. White cabinetry and light countertops provide a bright appearance, while decorative elements like a shelving unit and fixtures enhance the welcoming aesthetic. Natural light is allowed in through a nearby window.
Home in Porter
4.89 out of 5 average rating, 122 reviews

New Dunes Escape

Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

Guest favourite
Home in Michigan City
4.96 out of 5 average rating, 277 reviews

Visit LakeMichigan Beach-Brewery-Casino-OutletMall

Explore the beautiful Indiana Dunes National and State Parks. Book your stay at this cozy, newly renovated 2 bedroom home centrally-located for all your adventures. Within 2 miles of beach, restaurants, brewery, winery, casino, concert venue, spa, botanical garden, boat tours, kayak rental. Bonus trip: take the Southshore commuter train to Chicago for the day. Here, you can explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. 💙

Guest favourite
A bright living room is showcased, featuring a comfortable seating arrangement with a sofa and armchair. Natural light enters through large windows, illuminating the wood-tone flooring. A ceiling fan and framed wall art add to the welcoming ambiance.
Home in Porter
4.89 out of 5 average rating, 117 reviews

The Dune Den! Huge Yard/Firepit/Near Town+Dunes

Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Guest favourite
The open living area features large floor-to-ceiling windows framing views of the surrounding woods. A sleek two-tone sofa and modern armchairs are arranged near a minimal table. Warm wooden flooring complements the contemporary design, and a staircase leads to the upper level.
Home in Beverly Shores
4.96 out of 5 average rating, 230 reviews

Secluded Modern Retreat Near Beach - "Sandlot"

Stunning modern home overlooks private sand dunes on 5 wooded acres just a mile away from beautiful Lake Michigan beaches and surrounded by the Indiana Dunes National Park. Relax in our updated open-concept unique home nestled in the dunes. Enjoy the trails in the backyard, the friendly community, and local attractions near by. Just an hour to Chicago by car or the South Shore train is 1/2 mile from the house, with easy rides to Chicago and South Bend.

Top Guest favourite
The tranquil surface of Flint Lake reflects a colorful sunset, with soft hues of pink and orange blending into the serene blue sky. The surrounding tree line is silhouetted against the fading light, creating a peaceful and calming atmosphere.
Cottage in Valparaiso
4.94 out of 5 average rating, 450 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Escape the everyday with a relaxing stay at this cozy cottage located on Flint Lake! Hot tub, pontoon boat, fire pit, gas fireplace, tv, lake front, canoe, kayak, sauna, grill and more. This charming property is lake front with a small 50ft beach area and dock. Use of 2018 Sylvan pontoon boat, canoe, and kayak are included. You will love the lake life. Please note the pontoon boat is only available in season from May 1st to October 1st.

Popular amenities for Chesterton outdoor seating rentals

When is the best time to visit Chesterton?

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Avg. price$246 NZD$259 NZD$239 NZD$235 NZD$303 NZD$322 NZD$383 NZD$339 NZD$290 NZD$307 NZD$257 NZD$263 NZD
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Quick stats about holiday rentals with outdoor seating in Chesterton

  • Total holiday rentals

    Explore 30 holiday rentals in Chesterton

  • Nightly prices starting at

    Chesterton holiday rentals start at $152 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,880 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chesterton holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesterton rentals

  • 4.9 Average rating

    Chesterton stays are highly rated by guests—averaging 4.9 out of 5!